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Solution-phase parallel synthesis of 115 homosilatecan analogues

Gabarda, AE and Curran, DP (2003) Solution-phase parallel synthesis of 115 homosilatecan analogues. Journal of Combinatorial Chemistry, 5 (5). 617 - 624. ISSN 1520-4766

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Abstract

The parallel synthesis of 115 homosilatecans on 1-5 mg scale has been accomplished. Key reactions include N-propargylation of a common iodopyridone lactone with a silyl-substituted propargyl bromide, followed by cascade radical annulation with a substituted isonitrile. Simple manual techniques for parallel reactions were coupled with automated purifications (SPE, HPLC) to give high-purity final products. The speed and simplicity of the automated purification protocol more than compensated for yield losses in the synthesis of some analogues relative to traditional flash chromatographic purifications.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Gabarda, AE
Curran, DPcurran@pitt.eduCURRAN
Date: 1 September 2003
Date Type: Publication
Journal or Publication Title: Journal of Combinatorial Chemistry
Volume: 5
Number: 5
Page Range: 617 - 624
DOI or Unique Handle: 10.1021/cc030018g
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1520-4766
Date Deposited: 30 Jan 2014 18:11
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/20429

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